


Bewigged, Bothered, and Bewildered

by TopfSecret



Category: Actor RPF, American (US) Actor RPF, Real Person Fiction
Genre: Bottom Frank Sinatra, Coming Out, Crack, Crack Treated Seriously, Established Relationship, Flashbacks, Fluff and Crack, Insecurity, M/M, Mood Whiplash, Non-Explicit Sex, Non-Graphic Smut, Reader-Insert, Shopping, Trans Character, Trans Male Character, Transitioning, Two Shot
Language: English
Status: Completed
Published: 2020-02-11
Updated: 2020-09-17
Packaged: 2021-02-27 10:53:42
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,044
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22475938
Author URL: https://archiveofourown.org/users/TopfSecret/pseuds/TopfSecret
Summary: After a day full of reminiscence, your partner Frank takes you - in the guise of a valet - to buy a hairpiece or two. This has got to be the weirdest date you've ever been on.-----Frank Sinatra/Trans Male Reader. A fluffy crackfic with tender gay love. (Unfinished, but there is an outline of what happens in the end! ;D)
Relationships: Frank Sinatra/Reader
Comments: 14
Kudos: 11





	1. Why Frank Sinatra is a Cut Above the Rest

**Author's Note:**

> (Summary subject to change.)
> 
> I tag it as "crack" due to the "shopping for hairpieces" premise and mood whiplash, not because of the reader's transness.
> 
> The story is set in... up to you, really, but to me, it's between 1957-1963* to fit the fact that he sang Bewitched there. And also... you know... the premise really isn't a thing you can set in the 1940s where he still has lots of hair. xD
> 
> The reader is only out to Frank, is pretty gender-conforming for the era (and a top, just cause) and is 40-ish years old. I want to practice writing older characters, so please bear with me. Also, I took so many artistic liberties with the setting, I'm sorry, haha.
> 
> *You can choose based on your favorite Frank look/persona/etc.
> 
> Warnings: Period-typical transphobia, old-style queer language, implied violence, body/gender dysphoria, transition-related worries, makeouts, non-graphic sex, including PIV, implied smoking.
> 
> Without further ado, enjoy the fic!

The second hand of the clock ticks by. Every shift weighs your heart down, and the cool air of autumn doesn't help with your lethargy. The longer you wait for your boyfriend, the longer your sighs become. Still, a small laugh escapes you at that, a shudder in your gut while you sit right behind the island in front of Frank's spacious kitchen. Calling Frank your "boyfriend" always does. After all, you're both above forty. Where is the "boy" in that?

Nowhere, that is. You're a (relatively) long-lived man who's accomplished quite a bit, one of them being a director on part of his 1957 TV show, where you both met.

There was something in Frank that drew you in, despite his constant tardiness and insistence on doing only one take. (So unprofessional! So arrogant! But you'd always been attracted to cocky men.)

Despite his mercurial temperament and that one broken table in his changing room. He wasn't particularly (or even remotely) nice to you, of course he wasn't. He loved blaming the directors for low ratings. (Although he was nice to the janitors, to the cooks, to the musical crew, and the makeup artists. In his very Sinatra-like, impatient way.)

But his commanding presence, his intense gaze… You couldn't (still can't) help but drown in that deep, deep blue eyes, knees turning into jelly. His speaking voice, rough from smoking, drew you in with the intoxicating blend of attraction and envy, and his singing… there was no question on that. His rich baritone, his way of making a story out of a song, was practically was a flute right out of Hamelin, custom-made for you. And he seemed to know everything - he even knew you were eyeing him!

You, the "first woman" to direct such a high-profile TV show. A grand achievement, if you were a woman. Bitter guilt reared its ugly head when people started interviewing you for that, because it filled you with shame when it "should" fill you with pride. What did, however, was the fact that Frank fucking Sinatra had his eyes on you too. You. Who had nothing special aside from your "first woman"s, who was plain and shrill-voiced, who had your hair cut as masculinely as it was socially acceptable, who stood with lips in a straight line and your shoulders squared.

It attracted him even more. He'd walk up to you in the shadows of shameless advertisement plaques that say "Songs for Smokers Only" (spoofing _Songs For Young Lovers_ ' album cover), and whispered of how handsome you are, with your hair curling at the base of your neck and just above your ear. He'd lean on your shoulder and lay his full lips on your neck and your jaw, nibbling and sucking until he left a mark.

Your mother had always told you not to trust a man's sweet-talk, not to live off satisfying him. She told you a woman should be strong enough to live for herself.

But you're not a woman, and so, you let Frank sweep you off your feet. Even after his show ended, you'd visit each other. You'd return his kisses, lips crashing into him with hunger, tongue tasting him with a ferocity unprecedented. His jolt of shock invigorates you. Warm hands on your back, under your shirt. You'd pull him closer. Pushed him onto the bed. His eyes would always go so wide at that, but the brilliant blue would quickly darken with lust when you go down on him and take him in, his warmth inside you sending sparks all over your body. It made what had felt wrong, felt right.

And he, too, felt right in your care. He cooks for you, yes, and gives you gifts, but it's you who holds him in the vast loneliness of his home, who chases away his nightmares. It's you who wipes his tears, and caresses his face, and listens to his laments of old flames long extinguished. And as you gaze into his sad eyes, into the hard shell protecting his fragile heart, you learn that Frank Sinatra isn't a man who desires to dominate his lovers. He can't do that. He's assertive, but he craves for direction. He's confrontational and talks about surface emotions, but he craves intimacy. And you have plenty of that here.

It was a challenge in the beginning of your partnership, to convince Frank you're a man and not just a woman who leads in bed. But you explain to him how you've felt like this for as long as you remember it. That you have a man's soul, like he does, and is trapped in a woman's body that doesn't cooperate with you. And that you like men, too - yes, men like you can be homosexual too. There are many examples, you say, citing the queer rights movements blossoming around you. And last but not least: "I hope you're not straight, Frank."

At that, he chuckled, hearty and deep, you feel a vibration under your palm on his chest.

Your heart skipped a beat. A thousand scenarios of failure flashed in your brain, and stiffening, you thought: you had him in your hands, literally. It would spell doom for you to try to push _the_ Frank Sinatra onto the backrest and bash his head in, but you could move your hands away, get ready to jump off from his straddling you and never come back.

He felt you go rigid, though, and apologized. "I'm sorry, dear," he said, caressing your hair, "I didn't mean to laugh _at_ you."

Your vision, you realized, started blurring with tears, so you blink them back. You shouldn't be crying like this. You already had escape plans in case things go south. "So why?"

"Ya know why I wear this ring over here?" he asked, raising his little finger. It was, as ever, adorned with a ring, this time a nice gold with a deep red stone.

You furrow your brows. "Because you're Italian?" That was obvious.

"Of course, love, but also because it's a code for men who want to bed other men. Especially a man like you." Frank smirked, deepening his smile lines, crinkling the corners of his bright eyes. "That's why I laughed, baby. I'm not straight, my-" He paused. "If you're a fellow, you can't go by your old name, can you? That's a broad's name."

You flushed. No one had ever wanted to know your chosen name, until now.

"So what's your name, dear?" His voice was gentle now, and so was his finger on your cheek. "What should I call you now?"

The heat was spreading all over your body, and your chest is tight, but- but you blurt it out. No, no, that wasn't good enough. You repeat it, saying your new name firmly. Sending ecstasy in your head that explodes into a bright, unadulterated joy all over.

When Frank repeated it, and continues to call you by your chosen name again and again and again until you moved in and months after that, you thought you had never been happier.

* * *

"What are you thinkin' about?" Frank's voice comes in with its owner, breaking the spell of your reverie. He's smiling, leaning on the counter, resplendent in a black suit. It's familiar, from his pearly white teeth, to his bow tie, to the fragrance of lavender and cigarettes mingling with his natural scent. You almost feel the show set around you two again. The heat of the trysts when the cameras weren't rolling. The thrill, the kisses, the growing affection. The only different thing was the snap-brim hat on top of his head.

"Guess," you challenge, electricity charging your form. You're enjoying this, how your voice has deepened over the months from a combination of vocal training and hormone therapy.

He hums a noteless sound and takes a seat next to you. His presence is immediately warming.

"About me?" he asks. There is a twinkle in his eyes, teasing, but the sheer openness and want inside his gaze holds you close, like a blanket draped over your shoulders by someone you love. Like knowing you're not just _not alone_ , but also _not lonely_.

You smirk, leaning on one hand. "You know me too well, Frank." Your roguish expression softens, though, when he puts a hand on your shoulder. Heavy, warm. It touched the strap of your chest-binder, however. You flush as if you were set aflame.

Biting your lip, you take his hand in yours, cupping them with your smaller ones. He had such exquisite hands - not only good at unbuttoning shirts in the dark or playing a simple song on the guitar, but also just… a masterpiece of human cells. The firm, nicely-formed fingers. His short, manicured nails. The calloused palms that fit yours perfectly when you intertwine your fingers with his.

"Now, Frankie," you say, eyes roaming from his tan hands to his beaming face, "What are _you_ thinking? Are you thinking of me?"

Frank loosens as he chuckles. "Of course, darling." His tone implies an unfinished thought, though.

Maybe he needs a prompt. You lean closer to him, letting go of his hand to massage his thighs. "And?"

"Mmm," your partner hums. His taut muscles undo their knots, bit by bit, under the expertise of your fingers. "And I'm thinking of shopping, baby."

You stop your massage, eyebrows shooting up to your forehead. "We just went shopping two days ago, Francis." Sure, you liked what he'd bought you, but- "It's a bit excessive if we go again today. I already have three pairs of in-soled dress shoes. I have clothes non-transsexual men would kill to have."

Frank's lips curled into a pout, petulant, making his cheeks look rounder (though not by much, considering his thinness). You have to resist the urge to squish and pinch them. "I meant shopping for myself," he says mock-sulkily, "Can't a fellow be a little self-indulgent?"

Laughter bubbles inside you; you let it out, throwing your head back. When you look back at him, it's with one raised eyebrow and a lopsided smile. "What do you want, Mr. Sinatra?"

He sighs, shoulders sagging. "I don't _want_ anything. I _need_ a new hairpiece."

 _I can't believe this._ _(But it made sense; he's wearing a hat at home!)_ "You already have…" You rack your brain for an answer. In the car, on the wardrobe, come on, _come on-_ "Twenty of them, Frank. Maybe even more."

At your unamused expression, Frank makes a face again. "You know I can't use the same ones all the time, honey," he whines, "And many of them are spares anyway." He straightens his posture again, voice lowering seductively. "Come with me, baby, I'll get you something too."

You freeze at the implication he's making.

"I think you're worrying too early," you grit out, hiding the conflicting emotions threatening to burst out the pores of your skin, "It's only been a few months. The hormones haven't kicked in enough for that."

Frank scrunches his face, probably trying to remember the 'Effects of Testosterone' list. When it clicks to him, he gazes sadly at you, left hand brushing along your cheek, your still painfully-rounded jaw.

"Oh, sweetheart," he says, soft as a feather, "I'm sorry. I didn't mean to imply you'll lose your hair like I do."

He pauses to let his other hand caress your right cheek, moving down with the other down to your neck, down to you shoulder. A shiver runs down your spine at his touch. "I meant I'll buy you dinner afterwards. Or maybe some sweet cufflinks," he adds thoughtfully, "Or both."

You make a sound that's between a groan and a sigh. Of course he didn't mean that, you berate yourself, why were you so worried? And why do you have butterflies in your stomach at the prospect of shopping for fake goddamn hair with your partner, of all things?

"Love?" his hands move to your biceps, gently massaging your rigid form. "Are you okay?"

You gulp, trying to swallow, to digest those butterflies. Deep breaths. In… out. In… and out. "Yeah," you say firmly, forcing a smile as you jump down the stool, "Let's get you some hair, Francis."

Frank grinned, getting to his feet as well. "And let's get you changed, dear."

A cold pit cleaves your heart in two at his words. Of course. You have to dress like a woman if you want to be seen with him as his date. Dread fills you from the tip of your toes to your head- the wig over it, covering your trimmed hair and falling over your narrow shoulders- the bra making your chest stand out- the dresses, so tight around your waist- the makeup, oh, the makeup, and the _heels-_

"No, darling, not like that," Frank's hug - a hug? - snaps you back to the real world. You're confused, but you return his embrace anyway, arms snaking under his armpits and around his back. Then he pulls away slightly, head tilted down. The brim of his hat pushes against your head just a little. "You're not gonna be 'Lady Sinatra' anymore - you're going as my valet."

Your eyes almost pop out of their sockets. "You mean-?"

"Yes, dearest," Frank smiles, squeezing your torso, "I realize how sad you look whenever we had a date and you have to dress like a broad. It makes me sad too. You don't have to do that anymore, alright?"

Tears glisten in your eyes, burning and blurring your vision, but you blink them back, letting them flow onto your cheeks. The cheeks stretched by a gasp-turned-smile. "Thank you," you breathe out, hugging him even tighter, closing every bit of distance between you two, "I love you, Frankie. I love you so much."

He hugs you just as passionately, stroking your back in the way he knows is your favorite. "I love you too."

And when he says your name again, peppered with more declarations of love, your euphoria is greater than when he said it the first time.

**Notes for the Chapter:**

> Thank you so much for reading this fic! <3
> 
> I am a nonbinary and genderqueer trans person, and not a native English speaker. I'm aiming to make Frank maybe a bit of a clueless cis boyfriend who tries his best. He researches and helps Reader a lot, but of course doesn't have the trans wisdom. Still, I hope he doesn't come off as too insensitive while still being in character.
> 
> If any trans boys/guys/men, Sinatra aficionados (who's been in the game longer than me), or English-speaking peeps reading this have any corrections for me, please let me know in the comments! I'm working on the next/last chapter, so stay tuned ;)
> 
> Or if you have any other stuff to say, be it compliments, hate mail, and/or requests? You can say them too. See you in Chapter 2!


	2. Announcement

**Summary for the Chapter:**

> This isn't really a chapter, just an announcement.
> 
> (TL;DR: This fic is unlikely to be finished, I'm really sorry.)

**Notes for the Chapter:**

> warnings: mention of abuse and current pandemic, discussion of death and grief.

Abusive parents + grieving my dead friends (who also inspired this fic) + pandemic + chronic illness and disability + uni = not emotionally able to finish a fic, sorry.

**Notes for the Chapter:**

> Thank you so much for reading this announcement, and for your support of this fic so far <3
> 
> Next chapter: Commentary of the unfinished text. See what I wrote before the world imploded on me! :D
> 
> Thank you, and please take care, everyone.
> 
> TopfSecret


	3. A Tale of Love and Hair Loss / Toupée Tribute to Your Lover

**Summary for the Chapter:**

> The date finally arrives.
> 
> An unfinished chapter with commentary! :D

I planned for there to be three "meat" (as opposed to "filler").

Here goes!

**Chapter 2: A Tale of Love and Hair Loss**

1\. Dressing up Reader as the valet, which would be gender-affirming and makes him euphoric, also obviously lots of close-quarter touching and tenderness because! Putting on clothes on the person you love! Maybe even with a classic mirror scene?

I've written this, only this.

> You stand in front of the bedroom's full-length mirror, Frank right behind you. He has his hands on your shoulders, massaging them.

I didn't finish it because I discovered I don't really like this kind of scene for very personal reasons.

* * *

2\. The date, which is Reader and Frank going to the wig store and getting the hairpieces, which he at first is distracted about (he just stares at Frank and looks around store), but then Frank asks him to help put on the hairpiece? And admiring Frank? And Frank admiring him so much? And it's so intimate I can't 😭😭😭

Unfortunately, it never got to that point. It started out awesome, though! Who else would describe a _wig shop_ in such detail? :p

> Your destination is nothing like any place you’ve seen before. (Probably because you still have a full head of hair, but that's not the point.) It’s not exactly a dumpster, but it’s definitely less luxurious than you’d imagined your lover’s taste would be. And infinitely more fascinating, just like how Frank himself is.
> 
> You can see him aching to say “After you” as usual, but in your disguise, all he could do is pout and lead the way. You fall into step behind him, just a bit at his left side, so you can look at him. There he is, with his single-minded determination. His gaze is already to the woman waiting for him on one of the empty tables - the resident seller/wig expert, no doubt.
> 
> He takes a seat. You follow suit.
> 
> Okay, on second thought, this place kind of looks familiar. Like… a creepy jewelry store, mayhaps. Mannequin heads line the shelves adorning the walls. Their empty eyes seem to follow you as you admire the mops of false hair on the crown of their heads. They came in all sorts of colors - from inky black to whipped-cream white, from a sensible brown to striking greens and soft pastel pinks. The lengths were different, too - when you step in, it takes all of your willpower not to touch the auburn curls cascading down the shoulders of a lower-shelf wig stand.
> 
> And all the products on the tables! Shampoos and conditioners, brushes and powders, mirrors with a plethora of magnification choices - all of them are so neatly-arranged it puts Frank’s hyper-organized wardrobe to shame.
> 
> But it wasn't just the mannequins that offered a view. Hair extensions for women, long and wavy and sometimes in the shape of various updos, hang backwards on the walls. Chairs and stools are strewn along the floor so the seller can reach those hung the highest.

* * *

**Chapter 3: Toupée Tribute to Your Lover**

I know, this chapter title is hilarious. XD

3\. After the shopping trip, they talk about insecurities and vulnerabilities (in the car maybe?).

Like there'll be about Reader being "average" while dating a superstar, and him being trans while Frank is cis. Then Frank talks about being lonely and also about being insecure about his body (in a different way from Reader, who has been addressed in Ch. 1 and a bit of Meat #1), and there's a tender soft kiss and cuddling into the night... The mental image is causing me to melt in cuteness, tbh 💙💙💙

Honestly, writing extremely specific fantasies involving Frank Sinatra really butters my biscuits. Next time, I'm gonna make a self-insert, basically. Wheelchair user, nonverbal, trans, and so on. Because you know what? Marginalized people deserve these fantasies. We deserve to be loved, cherished, and worshipped in a healthy (and sexy as hell) relationship.

So see you in the next (Sin)atradventure! Thank you for reading, distinguished Frank fans! ;D


End file.
